Anal Experiences?

[tcitycity]

In recent days wife & I did our usual crossdresisng night out.
But this time it included my wearing my wifes skinny vibrator.

Basically once she finished chosing what to wear (and her doing my makeup and etc)... she inserted her toy up my butt and and we finished dressing.

Basically with it running for a while with brand new batteries... it was geting me hard rather quickly and made it difficult at times to avoid having my penis showing thru what I wore..

DOing this I actually got harder than i ever did (even as a teen), and actually came at least twice while still dressed up without her even touching me.

We finally got to a bar that is very secluded and its possible for us to litterally do just about anything we want... at this point she reached under the dress (it was nearly a miniskirt and started giving me one of the best bj's ive ever had... But she did this in a way that it looked like a girl was going down on a girl. To make it look more realistic I was in fact playing with my fake boobs and daresay I did a good job of acting on that part, while below there was no acting.


Wife estimates that I was at least halfinch to maybe 1" longer than ever before.

We left the bar quickly after I cam again, and by the time I got to the car I was fully nude and jerking off yet again.
We didnt make it to our home because my wife found a nearby park that was good enough for us to have a all out fuck.

This was a total of 4 times cuming and is a record in the shortest time for me.
And wife told me later that she had at least 3 orgasm and one more on the way when I drove instead.

But this drive was such that because she is very very flexible and could sit on my dick while I was driving, and still be able to see, it was very intense yet again.

But ultimately when we got home, a friend of ours that we often do stuff with was there waiting (he has a key to our place for various reasons)... and we caught him watching some of our porn... but he noticed we were both nude and continued jerking off.

WIfe went ahead and mounted him, and I entered from behind.

Ended pretty good, since we were already on our supercouch it can double as a bed and we all just stayed there and fell asleep. with both of us still in her.

[MasterCA]

If I am in the mood I will finger my ass or use the end of an old tooth brush (no longer using, obviously) with lube.

[tcitycity]

well our usual weekly outing in crossdress or related is now often combined with anal related.

Wife however, in order to get me to wear a dildo more often, is now having to do it herself...except that I go for both ends on her.. .

But we now vary on whether its a dildo or something else..
Often the something-else is soft stuff ..like a banana or similar.
FOr her that works well and she gets turned on.. it hasnt yet worked for me, as
it has to be vibration or real, at least so far.

[momo]

I am a female (in case you didn't guess already d...

And yes I have had anal sex and I have iced ice and other objects anally while masterbating, but I won't get into details d:

[davgrant]

I have like anal sex. Not recieving though Fingered myself a few times and a few objects while masturbating.

[cara.loverin1989]

Like Jaime..... Ocasionally.

[Aivey]

No, i've never actually had any experience. I only stuck my little finger up there once... It hurt a bit, and then i stopped...

[josh03]

yes ive used up to 4 fingers, pens, bananas, rolling pins and not only while masterbating, havent recived it yet but would like to

[KrazyFK]

I do it to myself quite a lot while masturbating. Up to 4 fingers, pens, candles. Once even a banana, but I had to be careful I didn't squash it, so it didn't stay in very long.

[tcitycity]

WHats the longest you kept anything (whatever it is)... in your butt?

Dildo or similar:
Wife: 1.5 hours max - it gets her going and cant handle it too long.
Me: somewhere in the 2-3 hours range and usualy either crossdress related or party dare related.

Human:
Wife: overnight sleep, with me in her.
me: overnight sleep, with a guy in me, and me in the wife.

[Memories for Life]

I was at a party (4 girls/4 boys + me) when we were all 15 years old and I got the dare to be blindfolded and stripped by the girls! Once I was naked, it must have been setup in secret because the other guys grabbed me and held me down on the coffee table while the girls handcuffed my hands and knees to the legs of the table. They pulled the blindfold off and were laughing and said "now the real entertainment can begin!"

The game was which girl could make me cry by hand. Each got 1 minute at my ass but I was pissed they tricked me into this situation so I keep a stern face! They even tried squeezing my balls until I thought they would burst but I stayed strong all the way thru the last minute! The guys were cheering because if I didn't cry, they all got blowjobs from the girls. After the girls were finished having to swallow cum, they were really mad at me. They said "now the boys get to try and make you cry!" If you do cry, the boys get to fuck us! If you don't cry, they have to eat our pussies! We're virgins and we want to stay that way, so you better not cry! If you do cry, after the guys leave, we'll really have fun with you!"

I was determined again not to show any weakness so I prepared for harder slaps on my already sore ass. I wasn't prepared for the guys using their belts to whip my ass! I made it thru 2 minutes of agony feeling like the skin on my butt was being peeled off. The 3rd guy must have been really horny because he decided to hit my balls hard with the belt. After the 5th direct hit, I was crying like a little baby! The guys were cheering and the girls all were cussing at me! After the girls had lost their cherries to each of the boys, the boys all left, feeling good and saying to me "hope you have fun now, bro!"

The girls came back to me and I could see cum and blood dripping from all their pussies. They said "now you get to do cleanup while you get to have fun!" The new game was that each girl would have their pussy cleaned of all the boys cum and their blood until the girl orgasmed. At the same time, the other girls would be trying to make me cum any way they could. If I could make it thru all 4 girls without cumming, they would let me go. If I couldn't hold out then I would be losing my virginity tonight!" Knowing exactly what they meant, I focused hard at thinking of the nasty slop I was eating out of these girls pussies. I made it thru 3 girl's orgasms even though I was rock hard from the girls trying to "milk" me. When the last girl pussy cleaning/stroke combo, they said "we made a promise to a friend for them to take your virginity so you're gone to cum this time!" I tried my best to get the girl to orgasm but when the other girls shoved their fingers in my asshole, the floodgates opened on my cock and I came in buckets! The last girl finally orgasmed and they all cheered!

They told me "our friend is ready to take your virginity now! Don't have too much fun because we're going to get all our friends to take your asshole!" I thought for sure that they were bringing a football player or other big athlete to fuck me. What freaked me out was when I felt fur on my hips and a heavy panting over my back. The girls had brought in a German Shepard and they help him mount my butt and slide his slimy dog cock full thrust up my asshole. As I learned later that night, the dog fucking was light in comparison to the girls other "friends" -- a mastiff, a goat and a horse!

[tcitycity]

We hosted a swinger party tonight.
Basically it was a gameparty and we pretty much previously stated there was to be no limits of any kind for either male or females.


The game we played was one we bought a adult store source, and was specifically for wide open swinging.

Because of my property being what it was, it was easy to have this game outside on our mostly secluded porch area.

The game basically gets you nude in a hurry, and everybody was itching for that.

The party was 5 couples. And all but one couple were very well built and in shape... The one couple were not obese but were slightly plumpy but AOK with us... as long as its not too much I could care less.
Our basic rule is that if we can reach all the way around, or if they can easily reach behind then it doesnt matter.

The game had the usual, kissing, basic petting, heavy petting, Jo, and etc... and there was maleonmale and girlongirl too.

The usual fun, was pretty much going on, and pretty much the goal was for everyperson in the party to pretty much get the same action done to them, before we would stop playing.

The game overall lasted 5 hours total (minor breaks for snacks and related).

Focusing on anal, each person be it girl or guy got anal action.
Depending on the game cards, it defined what anal would be.
Sometimes it was a choice, sometimes not a choice.
If the victim didnt choose then the person doing it to them chose.
In all cases, though, the point was to get the guy hard, and potentially not quite orgasm.
Purpose was that once the gf/wife of that guy stated he was ready and really hard, then the next round was obviously that guy as the victim, and get him off based off the card itself.

I ended up being the one who got stroked the most but pretty much the same amt of anal as the other guys. (Handjobs were on me the most because I tend to be the longest in the group when hardest).


Each of us pretty much got anal both via penis or dildo.

There is a socalled final round to the game, which basically is orgy.
So that was at times a variety of who & what.

[thomas]

ive done things from a finger to a shower handel but i realy want a cock up there

[heishere]

Yes I have. Eveything from felt markers to walnuts to the handles of toilet plungers has been up there.

[tcitycity]

Wife is wanting to celebrat her being nude at a all time amt...by basically doing whatever she thinks about to me..


since I tend to be nude around the house (as does she also)... its not hard to consider what to do.

Bsically wife today wanted to be anally fucked as long as possible wheterh via me or dildo or strapon (renter)..

Goal here was to see how long she could go with having somethin up there and how often she would have orgasm.

Even while asleep I made sure she had either me or a smaller dildo in her.

AS far as I know, she had something in for nearly 16 hours (including sleep).
She is shooting for 24 hours, but she may need to go to bathroom before it gets there... (time will tell)>